Gloucester

Historic Dogtown: A Walk Back in Time

Hike the trails of Dogtown in Gloucester Massachusetts with Cape Ann Museum

On Cape Ann, the name “Dogtown” conjures up many things — vast woodlands and trails; stone walls and cellar holes; tales of witches and widows; an ill-fated bullfighter; pastures, picnics and blueberries; a sea of rocks. Dogtown is all of these things and more. But first, it is a place where proud people once lived and worked, at the center of Gloucester, for nearly 150 years – until it became “Dogtown” and died out.

When: 
Sunday, June 1, 2025 10am-Noon
Location: 

The Backyard Growcery

Join Backyard Growers at Burnham's Field in Gloucester Massachusetts for a weekly Farmer's Market

Stop by Gloucester’s new weekly farmers market, the Backyard Growcery, managed by Backyard Growers. The Backyard Growcery is located at Burnham's Field, an urban park near Gloucester’s thriving waterfront, and features small-scale North Shore farmers, bakers, a seafood vendor, an artisanal pizza maker, and more, throughout the season.

When: 
Thursdays, June 18 - October 15, 2025 2:30-6pm
Location: 

Saint Peter's Fiesta | Saturday

A highlight event at St. Peter's Fiesta in Gloucester, MA is the infamous Greasy Pole contest near Pavilion Beach

The Saint Peter's Fiesta is an annual festival in Gloucester, Massachusetts celebrating the city's fishing heritage, close-knit families, community, and religious traditions.  The five-day celebration includes a carnival, live entertainment, and unique traditional events like the infamous 'Greasy Pole' contest and classic seine boat races. The festival is proudly sponsored by the Italian-American fishing community of Gloucester, and has all kinds of family-oriented activities and events, making it a great early Summer destination weekend event.

When: 
Saturday, June 28, 2025 10am-Midnight

Full Moon Hike at Ward Reservation

Join the Trustees on a journey up Holt Hill under the light of the full moon at Ward Reservation in Andover!

Join the Trustees for an evening journey up Holt Hill under the light of the full moon. Together, we will trek up the trail as night falls, and gather at the top beneath the moon & stars. Enjoy the sights, sounds, smells, and unique tastes of evening in the magic of Ward Reservation. We will share stories and tales about the moon and its effect on people throughout time.

When: 
Tuesday, June 10, 2025 7:30-9:30pm
Location: 

Explore! North Shore – Trails Day Hike at Ravenswood

Giant boulders can be found all over Ravenswood Park. How'd they get there?

Join the Trustees to celebrate National Trails Day with a guided hike of Ravenswood Park in Gloucester. On this intermediate hike, you will enjoy a ~3 mile loop with moderate elevation gain, as you are guided up the rocky and narrow Ledge Trail up to a scenic overlook of the harbor and then descend via the broader and flatter Salem Road carriage path trail. You’ll pass through an old quarry, rocky trails lined with beech, pines, ferns, and rare wetland plants. This glacier-shaped landscape provides shelter for a variety of wildlife, look for scat, tracks and dens along the trail! Our naturalist guides will share the human and natural history of this property, including how the Trustees maintains the properties many trails for all to enjoy.

When: 
Saturday, June 7, 2025 10am-1pm
Location: 

Annual Plant Sale | Generous Gardeners

Generous Gardeners is having a plant sale just in time for the growing season in Gloucester Massachusetts!

Generous Gardeners is having a plant sale to just in time for the growing season in Gloucester Massachusetts! Join us for a Plant Sale on Stacy Boulevard on Saturday, May 17, 2025 from 9am to noon. The event will be held rain or shine. Locally grown plants plus dahlia tubers will be available for sale.

When: 
Saturday, May 17, 2025 9am-Noon
Location: 

Bluefin Blowout Family 5k to Benefit Alzheimer's Association

The Bluefin Blowout Family Fun Run in Gloucester Massachusetts raises funds to combat the diseases of Alzheimer's and all other dementias

On Sunday, May 18th, 2025, come to Stage Fort Park, Gloucester for the Bluefin Blowout Family Fun Run 5K, Presented by the Lyon-Waugh Auto Group - Benefiting the Alzheimer’s Association. Run, walk, or stroll from Stage Fort Park to Hammond Castle and back to Stage Fort Park for a 5K loop. Enjoy the beautiful Cape Ann waterfront and fresh ocean air while raising money for the Alzheimer’s Association.

When: 
Sunday, May 18, 2025 7am
(race starts at 8:30)
Location: 

Gloucester Student Arts Festival

Gloucester Student Arts Festival showcases multiple forms of art created by the students of Gloucester Massachusetts

Arts Fest is an annual celebration of the arts in the Gloucester Public Schools, a day to enjoy creativity, connection, and celebrating our students’ talents as a Gloucester community. It is led by the Gloucester Education Foundation in partnership with the Gloucester Public Schools, Cape Ann Museum (CAM), and a host of local arts and cultural partners.

When: 
Saturday, May 17, 2025 11am-4pm

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Art Academy Summer Program at Montserrat College of Art in Beverly MA

StoryWalk Series at Maudslay

“Magnificent Monarchs” by Linda Glaser Storywalk at Maudslay State Park in Newburyport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! “Magnificent Monarchs” by Linda Glaser is featured in this StoryWalk Series. Younger kids will love this gentle, richly illustrated children’s nonfiction book aimed at preschool–third grade...
7:00 am to 8:00 pm

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

Hampton Beach Master Sand Sculpting Classic

The Annual Hampton Beach, NH Master Sandsculpting Competition 2025
The fun starts when 200 tons of imported sand is dropped on Hampton Beach and the “Grady Bunch” starts pounding up the sponsor site. The entire area is illuminated for night viewing through June 23rd. Watch Greg Grady and “The Grady Bunch” build a mammoth Sand Demo Site. 
7:00 am to 11:00 pm

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
7:00 am to 7:00 pm

Music Together - Tuesday in Marblehead

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® of Salem classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45...
10:00 am to 10:45 am

Gloucester Gratis Days at Hammond Castle

Bring your kids to the Hammond Castle Museum in Gloucester Massachusetts during April Vacation
In keeping with John Hays Hammond, Jr's original vision for his seaside castle-home to serve as a museum offering the Gloucester community access to ancient works of architectural art, Hammond Castle Museum will offer Gloucester residents free, self-guided tours each Tuesday throughout the regular...
10:00 am to 4:00 pm

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm

Barnyard Story Hour at Appleton Farms

Kids can meet the barnyard animals and hear a story at Appleton Farms in Ipswich Massachusetts.
Barnyard stories really come alive when you get to see the main characters in real life! Bring the kids down to Appleton Farms for our farm-fresh version of story time. Explore the farmstead, visit our learning garden, see our cows and rabbits, and find a spot to play under a shady tree in our...
10:30 am to 11:30 am

Guided Tour | When Granite Was King!

Find out the story behind the history of granite quarrying at Halibut Point State Park in Rockport, Massachusetts!
Halibut Point State Park is also a granite quarry with a history that goes back billions of years! Over one hundred years ago, the Rockport Granite Company quarried granite stone here.
11:00 am to 12:30 pm

Manchester by the Sea Summer Concert Series

Summer Concerts happen at Masconomo Park in Manchester by the Sea every Tuesday through the Summer!
Come to Manchester Tuesday nights all summer for the annual Music in Masconomo Summer Concert Series. Each week from 6:00 - 8:00 pm a variety of Oldies, Swing, Rhythm & Blues & Classic Rock music will fill the air! Bring your family and friends, blankets and chairs, and dinner to enjoy a...
6:00 pm to 8:00 pm

Wednesday, June 18

StoryWalk Series at Maudslay

“Magnificent Monarchs” by Linda Glaser Storywalk at Maudslay State Park in Newburyport Massachusetts
Enjoy this pre-school StoryWalk® at your leisure with the younger set and combine reading and time in nature! “Magnificent Monarchs” by Linda Glaser is featured in this StoryWalk Series. Younger kids will love this gentle, richly illustrated children’s nonfiction book aimed at preschool–third grade...
7:00 am to 8:00 pm

Saugus Iron Works Park Grounds & Estuary Walk

Take a hike along the Saugus River Estuary ande explore the Saugus Iron Works Park grounds in Massachusetts
Learn about the natural world in Saugus while ecploring the park ground ast the Saugus Iron Works National Historic Site in Massachusetts.
7:00 am to 7:00 pm

Hampton Beach Master Sand Sculpting Classic

The Annual Hampton Beach, NH Master Sandsculpting Competition 2025
The fun starts when 200 tons of imported sand is dropped on Hampton Beach and the “Grady Bunch” starts pounding up the sponsor site. The entire area is illuminated for night viewing through June 23rd. Watch Greg Grady and “The Grady Bunch” build a mammoth Sand Demo Site. 
7:00 am to 11:00 pm

Maudslay in Bloom Self-Guided Walk

 Maudslay in Bloom self guided walk at Maudslay State Park in Newburyport Massachusetts.
Maudslay State Park in Newburyport, Massachusetts, offers a delightful self-guided walk that is perfect for families with children. The park's 480-acre expanse, once the Moseley Estate, is rich with historical charm and natural beauty. Families can embark on a self-guided tour through lush...
7:00 am to 7:00 pm

Babson Farm Quarry Self-guided Walking Tour at Halibut Point

Kids will enjoy this tour of the Halibut Point State Park and Quarry with a focus on its stone-cutting history!
Take a self guided tour at one of Massachusetts most beautiful locations!
7:00 am to 6:00 pm

Music Together - Wednesday

Marblehead, Beverly Farms, Hamilton, Salem, Peabody Music Together
Music Together® is a research-based music & movement program for infants, toddlers, preschoolers, and the grown-ups who love them. Music Together® classes make it easy for parents/primary caregivers to play a crucial role in activating their child's music development. Classes are 45 minutes...
9:30 am to 11:15 am

Swan Boat Rides in Boston Public Garden

Swan Boat Boston North Shore Parent, North Shore Parents Summer Activities Guide
The Public Garden may be one of the most ideal picnicking locations in Boston. Well-groomed and overflowing with tulips, cherry-trees, with willows cascading over the duck pond, the Boston Public Garden is a great place to relax during Boston's most beautiful season.
10:00 am to 4:00 pm

Sing & Dance with the Music Man

Sing & Dance with the Music Man Brian Doser in Hamilton visit Massachusetts
Come join the fun at Community House Of Hamilton & Wenham Monday, Thursday and Saturday mornings at 10am for 30 - 45 minutes of great music with Brian Doser! Sing and dance with the Music Man during a family concert, featuring familiar and original tunes, performed by local dad and musician,...
10:00 am to 10:45 am

Saugus Iron Works House Tours

Free Ranger guided tours of the Saugus Iron Works House in Massachusetts
Join National Park staff at Saugus Iron Works National Historic Site for a 30-minute tour of The Iron Works House.
11:00 am

Saugus Iron Works Tours

Free Ranger guided tours at Saugus Iron Works Colonial Industrial Site in Massachusetts
Join the National Park staff at Saugus Iron Works National Historic Site for a tour of the colonial industrial site. On select days, you may be able to stick around and witness pop-up molten iron pour, blacksmithing, waterwheel demonstrations, and take part in hands-on river stewardship activities.
2:00 pm
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